A gag order is serious, and this sort of high-school trick won’t fool judges for a minute.

What does he mean by “fool judges”? That they will consider the removal of a warrant canary to be a violation of a gag order? This seems like a surprising thing to be unclear about. How have courts not ruled on this yet?

As it stands, removal of a canary doesn’t give much information. If the government goes to court to seek a ruling against a company for violating a secret gag order that is confirmation that one actually exists, and other information may be gleaned as well.

Alternatively: how do we know that a secret court hasn’t issued a secret ruling that says removing a warrant canary is illegal?

I’m waiting for somebody to really push the boundaries. Imagine if Reddit had a banner on the bottom of the screen saying “your account has not been the target of a warrant or subpoena.” One day they remove it…

Yes, many lawyers think it’s trying to be too clever, in a way that judges aren’t likely to buy. If you’re prohibited from telling people you received an NSL, changing a file on your website that is set up as a pre-arranged signal to tell people you received an NSL will likely be interpreted as violating the gag order. Even though officially you’ve just stopped telling people you didn’t receive an NSL.

However, as far as I know there isn’t a solid ruling on it, at least not a public one. The reddit version is also slightly more indirect than actively removing a warrant canary, in a way that might or might not be legally different. Reddit didn’t actively delete a file or statement on their website, which is the classic kind of warrant canary. What happened instead is that they, in the past, had included a statement in their annual report saying that they had not been served a national security letter. This year’s annual report, among miscellaneous other things that are different in its format and content, doesn’t include such a statement.